Hello! My husband and I traveled through Italy in 2019 spending time in Rome, Cinque Terre, Florence and Italy with day trips to Pompeii and Sorrento. This June we will spend 7 days in Montalcino doing day trips through Tuscany. We then have another 7 days (Jun 15 - 22) to spend in Italy. We would like to see something new - preferably more authentic and less touristy - staying in 1, maybe 2 places, so we can really soak up the day-to-day life and enjoy the city or close by areas. We will return back to Rome late Jun 21st or early Jun 22nd. I am looking for recommendations, please and thank you.
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I am an Umbria virgin, but it makes perfect sense with your existing plans and goals. Depending on how far east you go, you could also dip in to Marche, which is wonderful. I stayed in Ascoli Piceno and Sassoferrato. We stopped by Fabriano, a pleasant town.
I am a huge fan of southern Tuscany, and that could work well also. I have stayed in Massa Marittima and Orbetello. These areas are hardly undiscovered but will feel like they are in comparison to Florence, CT, etc. Early June should not be too crowded at the coast yet.